"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
"Beautiful inn. Staff were all very friendly and helpful. Room was very comfortable. Food from the restaurant was delicious, and the breakfast served was great as well. The fireplace in the tavern was a cozy touch and we enjoyed sitting by it. We will be back!"
"Beautiful inn. Staff were all very friendly and helpful. Room was very comfortable. Food from the restaurant was delicious, and the breakfast served was great as well. The fireplace in the tavern was a cozy touch and we enjoyed sitting by it. We will be back!"
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
Paradise Park offers diverse ecosystems around Lake Runnemede, with well-maintained trails through forests and meadows. Observe abundant wildlife including birds, turtles, and beavers in this peaceful natural sanctuary.
This working brewery offers a unique tasting experience with fresh craft beers and handmade pretzels. Enjoy the communal atmosphere in the taproom overlooking brewing operations or relax in the outdoor beer garden.
Housed in the historic 1846 Robbins & Lawrence Armory, this museum showcases America's largest collection of significant machine tools. Interactive exhibits highlight how precision manufacturing shaped our industrial heritage.
Vermont's first state park offers 12+ miles of trails through former quarries and historic homesteads. Drive the 3.7-mile auto road for panoramic views of the Connecticut River Valley without the summit hike.
The Path of Life Garden showcases 18 sculptures symbolizing human life stages across 14 serene acres. Wander through the hemlock maze and discover the Buddha statue overlooking a reflective labyrinth.
This community-centered library offers a welcoming hub for book lovers and local engagement. Browse their diverse collection or join one of their regular educational programs in this Ascutney gathering place.
This historic library has served as Windsor's community hub since 1882, offering diverse collections for all ages. Browse books, use free Wi-Fi, or join one of their engaging programs.
Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterward, savor craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.
I had a very comfortable stay. No complaints.
Many great cable TV channels, refrigerator, microwave, coffee maker, My room had a river view (pictured).
I had a very comfortable stay. No complaints.
Many great cable TV channels, refrigerator, microwave, coffee maker, My room had a river view (pictured).
Robert
Reviewed February 24, 2024Reviewed February 24, 2024
When I walked in the door I was dumbfounded with the size of the room, it was huge to call it a room does not do it justice. 2 stories, full living and dining room, you have to call it a villa, or a house I'd live in!
Clean comfortable, roomy, held 6 adults easily! Very new very modern, looked and smelled freshly renovated! Much more than I was expecting !
When I walked in the door I was dumbfounded with the size of the room, it was huge to call it a room does not do it justice. 2 stories, full living and dining room, you have to call it a villa, or a house I'd live in!
Clean comfortable, roomy, held 6 adults easily! Very new very modern, looked and smelled freshly renovated! Much more than I was expecting !
Jamie
Reviewed September 26, 2015Reviewed September 26, 2015
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
The pictures do not show how beautiful this property actually is. Looks 100 times better in person. They have a restaurant which is also very good. You don’t need to go anywhere else. The pool is a vibe after a long day of snowboarding. Recommend it 10/10. I will definitely go back again.
Ayleen
Reviewed February 12, 2024Reviewed February 12, 2024
Super Hotel it has been around since 1828. Lovely fireplace in the room and plenty of wood. You can actually see it in a Budweiser commercial. That tells you how pretty the locale is to experience. The service was nice as where the people. Woodstock proper is a 10 minute drive, so you definitely need a car but I found the location wonderful.
Super Hotel it has been around since 1828. Lovely fireplace in the room and plenty of wood. You can actually see it in a Budweiser commercial. That tells you how pretty the locale is to experience. The service was nice as where the people. Woodstock proper is a 10 minute drive, so you definitely need a car but I found the location wonderful.
Excellent service, beautiful building, must-have dinner and drinks and quality continental breakfast (who can beat that)
One thing to note that didn’t diminish experience is it is an old building and can be creaky at night so if you’re a light sleeper maybe consider bringing earplugs. Overall highly recommend though!
Excellent service, beautiful building, must-have dinner and drinks and quality continental breakfast (who can beat that)
One thing to note that didn’t diminish experience is it is an old building and can be creaky at night so if you’re a light sleeper maybe consider bringing earplugs. Overall highly recommend though!
Teddy
Reviewed January 24, 2022Reviewed January 24, 2022
We had an appointment at Dartmouth and this was the perfect place. We will certainly stay there again. I only wish we’d arrived there earlier in the day.
Quiet. Comfortable. And a fully appointed kitchen.
We had an appointment at Dartmouth and this was the perfect place. We will certainly stay there again. I only wish we’d arrived there earlier in the day.
Quiet. Comfortable. And a fully appointed kitchen.
This was a very nice and clean hotel. The front desk woman was very kind, helpful and even gave our girls candy when they got towels for the pool.
I have zero complaints except that the bathroom has the sliding barn door and it was not private AT ALL! Otherwise it was a great stay for one night.
This was a very nice and clean hotel. The front desk woman was very kind, helpful and even gave our girls candy when they got towels for the pool.
I have zero complaints except that the bathroom has the sliding barn door and it was not private AT ALL! Otherwise it was a great stay for one night.
Rebecca
Reviewed February 23, 2025Reviewed February 23, 2025
We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...
We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...
Outdoor Adventure: Windsor is a haven for outdoor enthusiasts, featuring exciting skiing opportunities and scenic landscapes.
Rich History: Explore historical attractions like the iconic bridge and nearby national state parks, perfect for culture lovers.
Vibrant Live Music Scene: Enjoy a lively atmosphere with local music performances, enhancing your après-ski experience.
Charming Downtown: Stroll through downtown Windsor, filled with unique shops and a friendly ambiance for families and friends.
Diverse Accommodations: Find a range of hotels, from family-friendly to pet-friendly, ensuring a comfortable stay.
Find great hotels near Windsor
Explore a variety of hotel accommodations in Windsor, Vermont, ideal for your vacation needs. Whether you seek adventure, a family-friendly environment, or pet-friendly options, Windsor offers a range of hotels to suit every traveler. Discover the best hotels, read reviews, and compare room rates to find the perfect fit for your stay in this charming New England town.
Super 8 by Wyndham White River Junction: This budget-friendly motel offers a comfortable stay for business travelers and pet owners alike. Located 19.3km from Windsor, Super 8 provides a welcoming atmosphere where pets are not only permitted but also enjoy complimentary amenities. Guests can take advantage of convenient services such as free Wi-Fi, a complimentary breakfast, and ample parking. The motel's straightforward accommodations ensure a hassle-free experience, making it ideal for those seeking practicality combined with comfort.
White River Inn and Suites: Perfectly situated 19.3km from Windsor, White River Inn and Suites is designed for adventure seekers and business travelers who appreciate inclusivity. This LGBTQIA-welcoming hotel offers a variety of recreational activities, including nearby snowboarding and skiing options, as well as bicycle rentals and Segway tours. Guests can enjoy spacious rooms with modern amenities, and the hotel’s commitment to adventure ensures an exciting stay. With its focus on community and adventure, this inn is a great choice for those looking to explore the great outdoors.
Best Western West Lebanon-Hanover Hotel: Located 17.7km from Windsor, Best Western West Lebanon-Hanover Hotel provides a family-friendly experience with a warm, welcoming atmosphere. This LGBTQIA-friendly hotel is equipped with amenities designed for guests of all ages, including complimentary cribs for families traveling with little ones. Business travelers will also find all necessary conveniences, such as meeting rooms and high-speed internet. With its commitment to comfort and accessibility, this hotel is an excellent option for families and business visitors alike.
Where to stay in and around Windsor
Windsor, Vermont offers a charming getaway perfect for outdoor enthusiasts and adventure seekers. Explore its scenic landscapes, vibrant downtown shops, and friendly atmosphere that welcomes families and history buffs alike. Just a short drive away, nearby towns enhance your experience with their unique vibes and excursions. Whether you’re skiing in the winter or enjoying summer activities, Windsor provides a delightful mix of urban charm and natural beauty for an unforgettable vacation.
Woodstock: Nestled 19.3km from Windsor, Woodstock is a charming town that flourishes with outdoor adventures year-round. While visitor numbers peak in the summer months of July and September to October, the town remains a delightful destination for skiing and various outdoor activities in the cooler months. Visitors can enjoy the local ski fields and resorts, while the picturesque surroundings include stunning lakes, majestic mountains, and the beautiful national state park. Whether you’re hitting the slopes or enjoying a scenic stroll, Woodstock offers a perfect blend of adventure and tranquility.
Cornish: Located just 1.6km away from Windsor, Cornish is a quaint city that attracts visitors primarily during the summer months from June to August. Known for its outdoor adventures and skiing opportunities, this small town is a haven for nature lovers. The local ski fields provide thrilling winter experiences, while educational attractions add a unique twist to your visit. Explore the nearby mountains, iconic bridges, and historic monuments that make Cornish a delightful place to spend your vacation, showcasing both natural beauty and rich history.
Ascutney: Situated within the Windsor area, Ascutney is a vibrant village that draws visitors throughout the year, with peak arrivals in the summer and fall months. Adventure seekers will find plenty to love here, as Ascutney offers exciting outdoor activities, including skiing at local resorts. The surrounding landscape is dotted with enchanting lakes, towering mountains, and access to the national state park, making it an ideal destination for nature enthusiasts. Ascutney's welcoming community and stunning vistas promise an unforgettable experience in the heart of Vermont.
Things to do in and around Windsor
Windsor, Vermont offers a perfect getaway for outdoor and adventure enthusiasts, particularly those interested in skiing. Visitors can enjoy thrilling activities at local ski resorts and fields. Additionally, the vibrant live music scene adds to the charm, providing entertainment after a day on the slopes. Whether you're hitting the trails or relaxing with some tunes, Windsor has something for everyone to enjoy.
Shopping
In Windsor, you can shop at The Sustainable Farmer for unique gifts. North Country Smokehouse, located 11.3km away, offers delicious local products. If you're up for a drive, visit Quechee Gorge Village, 17.7km from Windsor, where you'll find a charming selection of shops and souvenirs.
Recreation
The Upper Valley Aquatic Center offers a family-friendly atmosphere with swimming pools and fitness facilities, perfect for relaxation and fun. For golf enthusiasts, Woodstock Country Club provides a scenic outdoor experience, while The Strong House Spa specializes in rejuvenating body treatments, ensuring a blissful wellness retreat.
Adventure
Explore the Brownsville Trail for a refreshing outdoor hike, immersing yourself in nature. For winter sports enthusiasts, Arrowhead Recreation Area offers exhilarating skiing experiences only 14.5km from Windsor. For a unique adventure, Morningside Flight Park provides breathtaking scenic flights 17.7km away, perfect for thrill-seekers.
Nightlife
Experience the vibrant nightlife in Windsor by visiting Maple Lanes, an exciting arcadeAdventureZone just 12.9km away, perfect for some fun and adventure. For a more romantic evening, check out the Woodstock Town Hall Theatre or the Lebanon Opera House, both offering captivating cultural performances within a short drive.
*Distances are measured in a straight line; actual driving distances may vary depending on the route.
Booking tips and Expedia advantages for Windsor
For a budget-friendly visit to Windsor, Vermont, plan your trip between April to May or November for lower accommodation rates, avoiding higher-priced months like February and December. Tuesdays are the best days for cheaper hotel stays, while Fridays tend to be the most expensive. Use Expedia to compare room rates, filter for eco-friendly options, and book package deals that combine flights and activities for additional savings. Explore free local attractions to make the most of your trip without breaking the bank.
The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windsor are April to May and November, where the prices are slightly lower. This is in comparison to February, October and December, where prices are slightly higher.
The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Friday.
Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and eco-friendly accommodations currently available. To find the best prices and offers, simply arrange the price filter from lowest to highest.
Consider bundling your trip: You can save money by combining your hotel stay in Windsor with your flights and activities through an Expedia package.
Find the best attractions near Windsor
Windsor, Vermont, is perfect for outdoor enthusiasts and adventure seekers, offering a mix of thrilling ski vacations and rich historical experiences. Key attractions include the historic bridge, national state park, and environmental center, making it an ideal destination for families and culture lovers alike. Explore the scenic beauty and engaging activities that Windsor has to offer, ensuring a memorable visit.
Blow-Me-Down Bridge: This historic bridge, located just 805m from Windsor, offers a charming glimpse into the area's cultural heritage. Its picturesque setting makes it a perfect spot for photography and leisurely strolls.
Mount Ascutney: Situated 6.4km away, Mount Ascutney is a haven for adventure seekers. Enjoy hiking, breathtaking views, and outdoor activities that showcase the stunning scenery of Vermont.
Saint-Gaudens National Historic Site: Just 3.2km from Windsor, this historic site celebrates the life and work of sculptor Augustus Saint-Gaudens. Explore beautiful landscapes and immerse yourself in the rich cultural history of the region.
Best time to go to Windsor
The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.
Calendar Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
16.7°F (-8.5°C)
Light Rain
Mostly Cloudy
Average
Average
February
18.9°F (-7.3°C)
Light Rain
Mostly Cloudy
Slightly Low
Slightly High
March
27.1°F (-2.7°C)
Light Rain
Mostly Cloudy
Average
Average
April
39.4°F (4.1°C)
Light Rain
Mostly Cloudy
Average
Slightly Low
May
52.3°F (11.3°C)
Light Rain
Mostly Sunny
Slightly Low
Slightly Low
June
59.9°F (15.5°C)
Light Rain
Mostly Sunny
Average
Average
July
65.8°F (18.8°C)
Light Rain
Mostly Sunny
Slightly High
Average
August
64.0°F (17.8°C)
Light Rain
Mostly Sunny
Slightly High
Average
September
57.0°F (13.9°C)
Light Rain
Mostly Sunny
Slightly High
Average
October
45.5°F (7.5°C)
Light Rain
Mostly Cloudy
Average
Slightly High
November
33.1°F (0.6°C)
Light Rain
Mostly Sunny
Average
Slightly Low
December
24.3°F (-4.3°C)
Light Rain
Mostly Cloudy
Slightly Low
Slightly High
The nearest major airports for your trip to Windsor
When planning your trip to Windsor, Vermont, CONsider flying into one of the nearby airports. LEBanon Municipal Airport (LEB) is located 17.7km away and offers hotel options such as the 4-star Hanover Inn Dartmouth and the 3-star Hotel Coolidge, both providing convenient access. RUTland Southern Vermont Regional Airport (RUT) is 45.1km away, with nearby accommodations like the Killington Mountain Lodge. Hartness State Airport in Springfield, VT, is just 19.3km from Windsor, offering options such as the 4-star Inn at Weathersfield. Each of these airports provides easy transportation access to local hotels, ensuring a comfortable stay during your visit.
Frequently Asked Questions
What are some of the best vacation rentals in Windsor?
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home near Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Windsor.
If I need to cancel my hotel reservation in Windsor, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable as long as you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.
Where can I learn more about changing or cancelling my trip to Windsor?
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
How is it staying in Windsor?
Visitors can enjoy all that Windsor has to offer including the breweries, golf courses, and forests. The scenic and rural setting also entices those visiting the city. In Windsor, there are 21 hotels and other accommodations to choose from. Find out more about Windsor.
To venture out into the surrounding area, ride aboard one of the trains from Windsor Station.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.